Pros
The culture. I fully admit to drinking the Kool-Aid but darn, it's tasty and refreshing. "Use good judgment" really does cover most of our policies here. It's empowering and simultaneously encourages employees to really think about their actions. The people. They're smart, motivated, humble, and overall a great group. I joined HubSpot over two years ago with the promise of learning more than I had at any previous job, and I am still learning a ton. The perks. They keep getting better and better.
Cons
I feel disconnected from the non-engineering parts of the company. Within engineering things can be quirky/dysfunctional and if you can't adapt to the kind-of-weird ways we work (or have the moxie to effect the change you want to see) then you will not last long.